Advice: Is my lack of experience at 30 a turn-off?

I'm almost 30 and have never been in a relationship. I blame this on a number of circumstances, but let's be honest. At this point, half the problem is that I'm almost 30 and have never been in a relationship. Even if I think someone is attractive, mentally or physically, I can't seem to convey that I'm interested without saying something along the lines of "Me Jane, you cute." To make it even more fun, I'm active online the most, and while I seem to have flirting down there, finding people who aren't states away to flirt with in the real world is a gigantic hurdle. While I'm not opposed to online relationships or even long distance, I'd rather meet people in person before I invest time and emotion in a deeper connection with them. Any suggestions for portraying availability and interest without giving away my complete and utter lack of experience with the opposite sex and keeping it local?

Well, let me first say that you're not a lost cause, not by a long shot. I think you might be psyching yourself out a bit, though I can see why your lack of experience would weigh on you as you try to navigate the cluster[beep] of dating. But, honestly, any man worth his salt isn't going to be put off by the fact that you've never argued with a long-term lover at an IKEA. So no more of that defeatism, OK? If the vibe you're giving off is, "Eh, I'm okay," then dudes are going to perceive that and behave accordingly. You're awesome sauce. Own it.

Let me also say that the "Me Jane, you cute" line is a totally viable tactic for expressing interest. Sure, it probably wouldn't work on Foucault or anything, but he's dead and gay, so who cares what he thinks? When approaching someone you like, I think simple and to the point is always a winner. I wish we could all be a little more direct when it comes to telling someone we want to see them naked. Like, really, what is with this evasive and vague bull[beep]? Are we playing Mafia, or are we gonna bone? Just tell me so I can stop ordering these expensive vodka gimlets already! Many of my man friends have indicated they are thrilled when women approach them. So you're not going to lose any points for being proactive in pursuing people.

This brings me to flirting, which is a skill like any other. No one comes out of the womb with a smoking jacket and cocked eyebrow. (Except maybe William Shatner, oddly.) The more you flirt, the better you'll be. You've already got the wits, since you can do it with people online, now you just need the practice. Flirt with your waiter, the UPS driver, the guy with the cute dog at the park—whomever! The more you get used to talking to strangers, the more at ease you'll be when it's time to do so with someone you actually like.

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